Hydrochloric Acid → HCID 70173026, compound

HRID 2185448Notes

Reaction equation

HRID 2185448 reaction equation
[ClH:1].[O:2]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:41])[C@@H:17]2[CH2:21][C@@H:20]([NH:22][C:23](=[O:33])[CH2:24][NH:25]C(OC(C)(C)C)=O)[CH2:19][N:18]2C(OC(C)(C)C)=O)=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCOCC1>[ClH:1].[ClH:1].[O:2]([C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:41])[C@@H:17]2[CH2:21][C@@H:20]([NH:22][C:23](=[O:33])[CH2:24][NH2:25])[CH2:19][NH:18]2)=[CH:13][CH:14]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131723251HCID 131723251, compound

Product 1

HCID 70173026HCID 70173026, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 4 N hydrochloric acid in 1,4-dioxane (8 mL) was added to a solution of trans-4-(N-tert-butoxycarbonylglycylamino)-N-tert-butoxycarbonyl-L-proline 4-phenoxyphenylamide (A, 249 mg) in 1,4-dioxane (8 mL) at room temperature. After stirring at room temperature for 1 hr, the reaction mixture was concentrated in vacuo. The residue was washed with ether to give the title compound (140 mg) as a white powder: 1H NMR (400 MHz, D2O) δ 2.61 (t, J=6.35 Hz, 2 H), 3.49 (dd, J=4.88, 12.21 Hz, 1 H), 3.84 (t, J=6.35 Hz, 1H), 3.87 (s, 2 H), 4.64 (m, 1 H), 4.78 (m, 1H), 7.09 (m, 4 H), 7.23 (t, J=7.3 Hz, 1H), and 7.46 (m, 4 H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. washThe residue was washed with ether

Sources & evidence

ORD record
ord-804c57aa168f4fb88085b4228dc3b309
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

Loading…